(The floors are tile and terrazzo, so it is easy to clean up spilled paint.)We haven't gotten an estimate on the painting from a painter yet. 

I could come up with a down payment for an investment property in a different state easier than my home state at prices are pretty high in the 300-400 k just for townhomes.

It's that simple.Doesn't hurt to have real hardwood floors and A/C as well.

Can you arrange for counters, floors, painting other “basics” without him tacking on his 20%?

Highly recommend looking into Baselane for your rentals.

Quote from @Stuart Udis: @Robert Ellis Location Location Location...There is limited land supply in markets with high demand and high barriers of entry.

I’m a realtor and investor in Indianapolis, and I’d highly recommend adding Indy to your list of potential markets.

I see Downtown is highly rated for young professionals but the crime rates look pretty high. 

This could significantly increase the sale price and net profit after selling.Pros of Selling: Immediate large cash flow that could be reinvested elsewhere (stocks, other real estate).

You are priced out of Scottsdale quite a bit, but you might find something adjacent which would provide some good opportunities.